I have session logging turned on. by default and clear it out "now and then". it's usually a waste of space, except when it isn't and saved your life.
It might be nice if you could limit to some timescale or size automatically but that could take a lot of work to do right.
I usually run through tmux integration so there is tmux's scrollback as well.
What would be really cool would be if on attaching, iTerm would allow the user to scroll back through tmux history.
Reading back through an old session log might be useful. mayne just adding a dialog box to allow the slelction of the file and a simple a window to read in the log as though it was scrollback..
whether that means importing the data from tmux or reading it a line at a time as the user scrolls up.
I don't believe that works now though I have been surprised a few times about things in scroll back.